Pyridine → HCID 33239760, compound

HRID 718219Notes

Reaction equation

HRID 718219 reaction equation
Cl.[NH2:2][CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].N1C=CC=CC=1.[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1>CN(C)C=O>[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:2][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:26])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 678794-Fluorobenzoyl chlorideHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)

Product 1

HCID 33239760HCID 33239760, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of diethyl aminomalonate hydrochloride (5.0 g, 23.6 mmol) in pyridine (7.64 ml, 94.5 mmol) and dimethylformamide (60 ml) was added p-fluorobenzoyl chloride (4.19 ml, 35.4 mmol). The reaction mixture was stirred at room temperature for 15 hours. After removing the solvents, the residue was redissolved in dichloromethane, washed with water, brine and dried over Na2SO4. After removing the solvents, the crude residue was purified by flash chromatography on silica (CH2Cl2/MeOH 30:1) to yield the title compound as a white solid (4.9 g, 70%).

Workup

  1. customAfter removing the solvents
  2. dissolutionthe residue was redissolved in dichloromethane
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. customAfter removing the solvents
  6. customthe crude residue was purified by flash chromatography on silica (CH2Cl2/MeOH 30:1)

Sources & evidence

ORD record
ord-7ebd1ab6228c4990884cd042c4725495
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

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